What is the simplest Debian Packaging Guide?

This is a good HOWTO for creating a basic .deb file. It is suitable for creating .deb files for personal use but not stringent enough if you want to the package to be included in Debian / Ubuntu - for that you should read the Debian New Maintainer's Guide and/or the Ubuntu Packaging Guide (which I believe you've already tried).

A good tool for checking your .deb file for compliance is lintian (installable from the repositories).

There were two sessions here in the Ask Ubuntu chatrooms.

The Basics of Packaging on Ubuntu (Packaging: Part 1)

Ubuntu Packaging for Launchpad PPAs (Packaging: Part 2)

What parts are you having trouble with? Although complicated, the guide seemed quite clear when I was following it.

Quick Summary:

• Extract source .tar.gz
• Run dh_make
• Edit debian files
• Run debuild

You can even use dpkg-deb for creating simple packages.

Here's a nice tutorial from Ubuntuforums.